How to lead through rapidly changing times

In a year of unprecedented challenges that 2020 brought, the mantle of the chief executive became even more weighty. In the span of six months, the one-two punch of the pandemic and racial injustice brought a reckoning to the role that no one could have predicted or prepared for. That meant that some succeeded based on the strength of their mission and the agility to shift course while others failed.

During the final day of the Fast Company Innovation Festival, deputy editor Kate Davis sat down with two CEOs who are thriving despite the challenges. Both Aaron Levie, cofounder and CEO of Box, and Jennifer Tejada, CEO and chairwoman of PagerDuty, helm unicorn startups and offered insights into how they view their roles and what opportunities lie ahead for their companies and their careers.

Tejada describes herself as an “extreme extrovert” who was always walking the halls (and is now doing that virtually by being present on Slack and in Zoom calls). She’s constantly seeking direct feedback, admitting that as CEO it’s often tough to get when employees tell her what she thinks she wants to hear versus what needs to be said.

For his part, Levie sees his leadership as essential to ensure the company is going in the right direction, which is even more important because of the current environment. “You are only as good as your organization and your team,” he says, so cultivating great talent is necessary to make sure the company has clarity to be decisive at key moments.

Both emphasized the fact that building a strong company culture has been a guiding light through a year fraught with uncertainty. Levie and Tejada agreed that their employees look to them to offer structure and transparency, even when they don’t have all the answers.

Tejada says she’s had numerous conversations with employees about engaging customers. “You cannot manage by aggregate,” she explained, “everyone is experiencing things differently.” That’s why she advises listening actively and empathizing. When checking on customers, she says, it’s not just about asking how the business is doing, they need to find out how the person is doing and how their family is doing. It’s helped that PagerDuty’s core values underscore these efforts, she says. “Connecting people to the company’s purpose ensures our vision is still well suited as the world rapidly evolves,” says Tejada.

Levie notes that agility has played a major role in his leadership this year. Building an organization that is flexible is essential when you can’t predict what comes next, says Levie, especially when you don’t have all the answers. “We hope we make the right calls,” he says.

The strength of their respective companies’ cultures has allowed them to flex to a part of leadership that simply didn’t exist even a decade ago. The political climate and civil unrest has been top of mind for them both, and each maintains that it’s important for a CEO to take a stand on issues like equality and racism. Tejada observes, “A culture will be defined by the lowest level of behavior tolerated, not the most audacious aspiration.”

As such, both have made concerted efforts to make their organizations more inclusive. As Levie says, “With the stark injustices in this country, even if there is no business implication, [we] have to make sure we are calling that out and doing our part to improve.”

That doesn’t mean they think they’ve got it all figured out now. Levie quips about making early decisions on remote work based on the thinking that the pandemic would be resolved in just a couple of weeks. But he stresses the point of being able to think quickly and be decisive. If he has any regrets as a leader, Levie says it was during “times where I didn’t have us move quickly enough on a major issue or strategy.” His aim now is to “improve the clock speed” of the organization to take risks and pivot when needed.

Tejada agrees, but adds that one of the times she dragged her feet was on her way up the ladder. “I waited too long to be CEO,” she confesses, and it took a mentor calling her an “idiot” a couple of times before she agreed to throw her hat in the ring. Now, she says, “I was born for this.”

Which is good timing because there’s no end to the current challenges in sight. Yet both Tejada and Levie see silver linings amid the crisis points. For Tejada, the excitement of possibility and innovation offer a positive jolt of inspiration and intellectual stimulation. And even though as CEO there is no downtime, she’s celebrating the fact that for the first time ever, she’s been able to have dinner with her family every night.

And Levie’s faith in the country, and in the world’s response to the most pressing social and economic issues, prevails. “There’s tremendous opportunity for new business models and new ways of working,” he says. “Some exciting positive things will emerge.”